[4-(2-Azido-5-methyl-3-phenylphenyl)phenyl]-trimethylazanium;trifluoromethanesulfonate | 1174572-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(2-Azido-5-methyl-3-phenylphenyl)phenyl]-trimethylazanium;trifluoromethanesulfonate
• CAS: 1174572-81-6
• 化学式: CF₃O₃S*C₂₂H₂₃N₄
• 分子量: 492.522
• InChiKey: HAQGJLHSIVCXGJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-(2-Azido-5-methyl-3-phenylphenyl)phenyl]-trimethylazanium;trifluoromethanesulfonate 在 辛酸铑 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 trifluoromethanesulfonate;trimethyl-(6-methyl-8-phenyl-9H-carbazol-2-yl)azanium 、 trifluoromethanesulfonate;trimethyl-[4-(3-methyl-9H-carbazol-1-yl)phenyl]azanium
  参考文献：
  名称：

  Examination of the Mechanism of Rh₂(II)-Catalyzed Carbazole Formation Using Intramolecular Competition Experiments

  摘要：

  The use of a rhodium(II) carboxylate catalyst enables the mild and stereoselective formation of carbazoles from biaryl azides. Intramolecular competition experiments of triaryl azides suggested the source of the selectivity. A primary intramolecular kinetic isotope effect was not observed, and correlation of the product ratios with Hammett sigma(+) values produced a plot with two intersecting lines with opposite rho values. These data suggest that electronic donation by the biaryl pi-system accelerates the formation of rhodium nitrenoid and that C-N bond formation occurs through a 4 pi-electron-5-atom electrocyclization.

  DOI：

  10.1021/jo901224k
• 作为产物：
  描述：

  2'-azido-N,N,5'-trimethyl-[1,1':3',1''-terphenyl]-4-amine 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以69%的产率得到[4-(2-Azido-5-methyl-3-phenylphenyl)phenyl]-trimethylazanium;trifluoromethanesulfonate
  参考文献：
  名称：

  Examination of the Mechanism of Rh₂(II)-Catalyzed Carbazole Formation Using Intramolecular Competition Experiments

  摘要：

  The use of a rhodium(II) carboxylate catalyst enables the mild and stereoselective formation of carbazoles from biaryl azides. Intramolecular competition experiments of triaryl azides suggested the source of the selectivity. A primary intramolecular kinetic isotope effect was not observed, and correlation of the product ratios with Hammett sigma(+) values produced a plot with two intersecting lines with opposite rho values. These data suggest that electronic donation by the biaryl pi-system accelerates the formation of rhodium nitrenoid and that C-N bond formation occurs through a 4 pi-electron-5-atom electrocyclization.

  DOI：

  10.1021/jo901224k

文献信息

• Examination of the Mechanism of Rh₂(II)-Catalyzed Carbazole Formation Using Intramolecular Competition Experiments
  作者：Benjamin J. Stokes、Kathleen J. Richert、Tom G. Driver

  DOI：10.1021/jo901224k

  日期：2009.9.4

  The use of a rhodium(II) carboxylate catalyst enables the mild and stereoselective formation of carbazoles from biaryl azides. Intramolecular competition experiments of triaryl azides suggested the source of the selectivity. A primary intramolecular kinetic isotope effect was not observed, and correlation of the product ratios with Hammett sigma(+) values produced a plot with two intersecting lines with opposite rho values. These data suggest that electronic donation by the biaryl pi-system accelerates the formation of rhodium nitrenoid and that C-N bond formation occurs through a 4 pi-electron-5-atom electrocyclization.